The Question Every Entrepreneur Needs to Ask in 2025 (It may be winter, but it’s always smart to weed out what is and isn’t working)

I want to share a little secret with you that holds the power to completely change how you run your business. It’s not some fancy system, a new app, or even a groundbreaking strategy. It’s way simpler than that. Ready?

Ask your customers what they want.

Yeah, yeah, I know. It sounds obvious. But here’s the thing: most entrepreneurs don’t do it. We think we already know what our customers want. We’re in our heads, strategizing and refining, convinced we’ve nailed it. And sure, you might be doing a great job. But the gold, the really game-changing stuff, isn’t in your head. It’s in theirs.

Why ask?

It may be winter, but it’s always a good time to weed out what is and isn’t working in your business. Years ago, I started asking my customers a simple question:
“What’s one thing we could do differently to better serve you?”

The first time I asked, I thought I’d get a few polite “Everything’s great, Mike” responses. What I got instead were some hard truths and incredible insights. People told me things I didn’t want to hear, like how one part of my process was confusing or how I wasn’t proactive enough in communicating updates. Ouch.

But guess what? Those insights were a gift. Once I made those changes, my business ran smoother, customers were happier, and word started to spread.

Here’s why asking works:

• You get out of your bubble: Run a business?? Then you’re too close to your work. You can’t see what our customers see.

• You find easy wins: Sometimes a customer comes back with a tiny tweak you can implement in a day that makes all the difference.

• You build loyalty: Asking for feedback shows your customers you value them. They’ll stick around when they feel heard.

The Pumpkin Plan connection

If you’ve read The Pumpkin Plan (and if you haven’t, what are you waiting for?), you know the magic of focusing on your best customers. Asking them for feedback is like giving your business fertilizer. Their answers will help you prune the stuff that’s holding you back and double down on what works.

One of my favorite questions to ask is:
“What’s one thing about our industry that drives you crazy?”

Why? Because this is where the aforementioned gold is. If something is driving your customer nuts, I guarantee it’s bothering other people, too. And if you’re the one to fix it? You’re now the hero of your industry.

How to ask (without feeling awkward)

Asking for feedback can feel awkward. What if they tell you something you don’t want to hear? (Spoiler alert: they will.) But trust me, the discomfort is worth it.

Here’s how to do it:

1. Start small: Pick 5 of your best customers, the ones you love working with.

2. Keep it simple: Ask just one question. Either:

   • “What’s one thing we could do differently to better serve you?”

   • Or: “What’s one thing about our industry that drives you crazy?”

3. Listen without defending: This is the hard part. Don’t explain yourself. Just listen. Thank them. Write it down.

4. Find the pattern: If multiple people mention the same issue, congratulations—you just found your next big improvement.

5. Act fast: Pick one idea and implement it. Show your customers you’re serious about making things better.

A real-life example

A reader who runs a home-cleaning business shared that he tried this. They asked their customers what drove them crazy about the industry. One client said, “I hate that I never know who’s coming to my house.”

Boom. Easy fix. They started sending out a “Meet Your Cleaner” email with a photo and bio before every appointment. The result? A 30% increase in repeat customers in just a few months.

This week’s assignment

Let’s make this actionable. This week, I want you to:

1. Pick 5 of your best customers.

2. Ask them one of the questions I shared.

3. Write down their feedback.

4. Choose one idea to act on and get it done.

That’s it. No overcomplicating, no second-guessing. Just listen and take action.

Permission to be human

You’re not going to get everything perfect. No one does. You’re going to miss the mark sometimes, and that’s okay. The important thing is that you’re showing up, listening, and improving.

So, what’s one thing you could do differently to better serve your customers? Go out and ask! The answer may just be the easiest fix – and THE step you need to work through your goals.

And hey, if this process feels messy or uncomfortable, good. That’s where growth happens.

You’ve got this. Let me know what you discover, I can’t wait to hear.

-Mike

PS – I mentioned The Pumpkin Plan. To get a copy of the book, you can visit your favorite bookseller or order it here. Want more help? Reach out to Pumpkin Plan Your Biz to learn how to implement the Pumpkin Plan strategies.

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